This invention relates to novel N,N-dimethyl-2-(aminosulfonyl)-3-pyridine-carboxamides. The compounds of this invention and their agriculturally suitable salts are useful as agricultural chemicals, and in particular, as herbicides which may be selective to corn.
U.S. Pat. No. 4,544,401 and U.S. Pat. No. 4,435,206 disclose herbicidal pyridinesulfonylureas.
U.S. Pat. No. 4,518,776 (Swiss priority 7/19/82) and EP-A-101,670 (Swiss priority 8/23/82, published 2/29/84) disclose, in part, a process for the preparation of compounds of formula ##STR1## wherein ##STR2##
R.sub.1 is, among other values, C(O)NHC.sub.1 -C.sub.4 alkyl or C(O)N(C.sub.1 -C.sub.4 alkyl).sub.2 ;
R.sub.2 is H, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
A is O, S, NR.sub.5 or --C.dbd.N--;
X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylamino or di-C.sub.1 -C.sub.4 alkylamino;
Y is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy; and
Z is CH or N.
U.S. Pat. No. 4,518,776 generically discloses but does not claim compounds of the invention. (No pyridine carboxamides are specifically disclosed.)
EP-A-107,624 (Swiss priority 10/25/82, published 5/2/84) discloses, in part, a process for the preparation of compounds of formula ##STR3## wherein ##STR4##
R.sub.3 is H, halogen, NO.sub.2, OCH.sub.3 or CF.sub.3 ;
R.sub.5 is, among others, CONR.sub.8 R.sub.9 ;
R.sub.8 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 cyanoalkyl, OCH.sub.3, OC.sub.2 H.sub.5 or C.sub.3 -C.sub.5 alkenyl;
R.sub.9 is H, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.5 alkenyl;
Y is O, S or C(R.sub.6).dbd.N; R.sub.a is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 haloalkoxy, C.sub.1 -C.sub.5 alkylthio, C.sub.2 -C.sub.10 alkoxyalkyl or C.sub.2 -C.sub.10 alkoxyalkoxy;
R.sub.b is the same as R.sub.a or NR.sub.c R.sub.d ; and
E is CH or N. This application generically discloses but does not claim compounds of the invention. (No pyridine carboxamides are specifically disclosed.)
U.S. Pat. No. 4,549,898 discloses herbicidal sulfonylureas of formula ##STR5## wherein
X is O, S, NR.sub.4 or C(R.sub.5).dbd.N;
Y is O or S;
Z is O or S;
E is N or CH;
R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkylthio, NR.sub.6 R.sub.7 or alkoxyalkyl containing not more than 4 carbon atoms;
R.sub.2 is, among others, CONR.sub.6 R.sub.7 ;
R.sub.3 is H, halogen, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or CF.sub.3 ;
R.sub.5 is H, NO.sub.2, F, Cl, Br, CH.sub.3, CF.sub.3, S(O).sub.n C.sub.1 -C.sub.3 alkyl, COC.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 alkoxy;
R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, methoxy or ethoxy; and
R.sub.7 is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl. Although compounds of the invention are generically disclosed, no examples of pyridineamides are listed in the tables.
EP-A-155,767, published 9/25/85, discloses, in part, herbicidal sulfonylureas of formula ##STR6## wherein
R is H or CH.sub.3 ;
R.sub.5 is H, CH.sub.3, Cl, Br, CO.sub.2 R.sub.15, C(O)NR.sub.16 R.sub.17, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 R.sub.18 or NO.sub.2 ;
R.sub.16 is C.sub.1 -C.sub.2 alkyl;
R.sub.17 is C.sub.1 -C.sub.2 alkyl;
R.sub.19 is CH.sub.3, Cl, Br, NO.sub.2, C.sub.1 -C.sub.2 alkylthio or C.sub.1 -C.sub.2 alkylsulfonyl;
X is CH.sub.3, OCH.sub.3, Cl, Br, OCH.sub.2 CF.sub.3 or OCHF.sub.2 ;
Y is C.sub.1 -C.sub.3 alkyl, CH.sub.2 F, cyclopropyl, C.tbd.CH, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.2 CH.sub.2 F, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CF(OCH.sub.3).sub.2, ##STR7## CR(OCH.sub.2 CH.sub.3).sub.2 or OCF.sub.2 H; and
Z is CH or N.
There is still a need for improved agricultural chemicals, especially herbicides which may be selective for corn. According to this invention, such herbicides have been found.